Director of Operations & Vendor Compliance

CharterUP

19d • $130,000 - $150,000 • Remote

About The Position

CharterUP is transforming the $30 billion group transportation industry with cutting-edge technology and innovative SaaS software, delivering an industry-leading experience for both customers and operators. Trusted by most Fortune 500 companies, our platform connects users to thousands of charter bus and minibus operators nationwide. In just 60 seconds, customers can access real-time availability, transparent pricing, and detailed vehicle options—whether organizing a corporate event, a company shuttle, or a wedding. By streamlining what was once a fragmented and stressful process, CharterUP brings transparency, accountability, and efficiency to an industry overdue for innovation
With CharterUP, group transportation is no longer a hassle but an elevated, reliable experience. Join us as we lead the future of group travel.
CharterUP is seeking a data-driven, execution-focused operations leader to serve as our Director of Operations and Vendor Compliance a critical role that will act as an extension of the VP of Service Operations. This leader will balance strategy with hands-on execution, independently analyzing data, building reporting in Tableau, and ensuring managers and teams execute consistently against KPIs. They will drive operational excellence, improve team capability, and free executive leadership to focus on enterprise priorities.
The ideal candidate thrives in complex, fast-moving environments, knows how to dig into data and insights directly, and can hold managers accountable while also shaping long-term strategy.

Requirements

• 8+ years of experience leading operations in high-volume service delivery, dispatching or contact center environments ideally within transportation, mobility, or other complex service industries where compliance, customer satisfaction, and vendor management are critical. The ideal candidate will have worked in vendor management in a 2 sided marketplace.
• Proven success managing frontline leaders and large teams in high-volume, high-stakes environments.
• Advanced ability to compile, analyze, and visualize data using Tableau, Excel, and Google Sheets—capable of building dashboards and reporting independently without reliance on a dedicated analyst.
• Strong track record of driving manager performance and holding teams accountable to KPIs.
• Ability to balance strategic vision with tactical execution, rolling up sleeves when needed to solve problems, build processes, and drive results.
• Vendor-facing communication and escalation management skills with executive presence.
• Highly organized, data-driven, and comfortable making decisions under pressure while managing both short-term problem-solving and long-term process improvements.

Nice To Haves

• Advanced ability to manipulate, clean, and interpret large datasets; experience with BI tools (Tableau, Looker, Power BI) and proficiency in SQL or other query languages strongly preferred. Must be able to build dashboards and explain analytical reasoning in detail.

Responsibilities

• Own the compilation, analysis, and visualization of operational data building Tableau dashboards and reporting frameworks to identify opportunities, monitor KPIs, and support executive decision making.
• Deliver actionable insights to executive leadership, ensuring data informs daily execution and long-term strategy.
• Serve as the VP’s operational extension—taking tactical execution and operational oversight off their plate.
• Drive cross-functional priorities with discipline, ensuring initiatives are executed with rigor and leadership bandwidth is preserved.
• Lead a distributed team of managers and supply specialists, ensuring leaders under you are aligned, supported, and held accountable.
• Set clear expectations, track performance, and consistently drive improvement against KPIs for productivity, efficiency, and SLA attainment.
• Identify and execute strategies to improve operational efficiency and margin attainment, including new tools, automation, and process redesign.
• Drive initiatives focused on reducing service failures and improving provider capacity through rigorous data analysis and continuous improvement.
• Build region-specific margin strategies through cross-functional collaboration with Service Operations and Data Science.
• Strengthen pricing integrity controls to ensure vendor pricing aligns with market standards and supports wholesale margins.
• Provide senior leadership to the compliance function, ensuring vendor adherence to company policies, contractual obligations, and operational standards.
• Oversee programs to strengthen delivery reliability and risk management.

Benefits

• Remote-First Flexibility: Work from anywhere we hire, with built-in flexibility. U.S.-based employees may reside in any of our 19 approved states.
• Comprehensive Health & Wellness: Medical, dental, and vision insurance, mental health support, virtual care, gym discounts, and family-building benefits. In the U.S., we cover 100% of premiums for employees. International benefits align with local standards.
• Time Off to Recharge: Paid time off so you can truly unplug. U.S.: 15 PTO days (increasing to 20 after 2 years) + 8 paid holidays. International policies vary by country.
• Financial Peace of Mind: Company-paid life, short-term, and long-term disability insurance where available.
• Performance-Driven Culture: Join a fast-moving, ambitious, and collaborative team that wins together.
• Referral Rewards: Earn bonuses for bringing top talent to the team.
• Planning for the Future: Long-term financial planning support. U.S.: 401(k) plan. International: region-specific savings programs where applicable.
• Top-Tier Tech: Choose a Mac or PC, plus monitor, keyboard, and mouse to hit the ground running.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed